EP2898021A1 - Dérivés de l'acide sulfosuccinique servant d'agent de dispersion dans des préparations de pigments exemptes de liants - Google Patents

Dérivés de l'acide sulfosuccinique servant d'agent de dispersion dans des préparations de pigments exemptes de liants

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Publication number
EP2898021A1
EP2898021A1 EP13753812.0A EP13753812A EP2898021A1 EP 2898021 A1 EP2898021 A1 EP 2898021A1 EP 13753812 A EP13753812 A EP 13753812A EP 2898021 A1 EP2898021 A1 EP 2898021A1
Authority
EP
European Patent Office
Prior art keywords
pigment
component
aqueous
binder
parts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP13753812.0A
Other languages
German (de)
English (en)
Other versions
EP2898021B1 (fr
Inventor
Hendrik Ahrens
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant International Ltd
Original Assignee
Clariant Finance BVI Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Clariant Finance BVI Ltd filed Critical Clariant Finance BVI Ltd
Publication of EP2898021A1 publication Critical patent/EP2898021A1/fr
Application granted granted Critical
Publication of EP2898021B1 publication Critical patent/EP2898021B1/fr
Not-in-force legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C09B67/0066—Aqueous dispersions of pigments containing only dispersing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C09B67/0066—Aqueous dispersions of pigments containing only dispersing agents
    • C09B67/0067—Aqueous dispersions of phthalocyanine pigments containing only dispersing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/0086—Non common dispersing agents anionic dispersing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/41—Organic pigments; Organic dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/45—Anti-settling agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic

Definitions

  • the present invention relates to aqueous, binder-free
  • Coating materials, lacquers, paints and their use for printing on two-dimensional fabrics such as paper, cardboard, plastic, textiles and leather.
  • aqueous, binder-free pigment preparations with organic or inorganic pigments are produced.
  • Pigment preparations come as tinting pastes in hardware stores and
  • Tinting systems aqueous and solvent-based paints and varnishes added to adjust to customer requirements corresponding shades.
  • tinting pastes typically contain pigment concentrations in a broad concentration range of 1 to 75 mass%.
  • An environmental seal involves the use of known wetting and dispersing aids, so that the skilled person is always on the look-out for new dispersants and combinations in order to produce liquid, stable, aqueous pigment preparations.
  • the present invention was based on the object stable and flowable, Produce alkylphenol-free aqueous pigment preparations that show no sedimentation of the pigments used over a longer period of time, and with which aqueous and solvent-based paints, lacquers and glazes can be dyed alike.
  • aqueous paints and inks in particular emulsion paints, silicate emulsion paints and aqueous silicone resin paints
  • the pigment preparations according to the invention should show no rubout problems.
  • aqueous pigment preparations should also be compatible with solvent-based paints, be homogeneously distributed by mixing, stirring or shaking in the paint and give a smooth, uniform color image when painted or rolled on surfaces.
  • the compatibility of the aqueous pigment preparations is also checked by the rubout test described in US Pat. No. 3,840,383
  • Another object of the invention was to provide aqueous pigment preparations with low human-toxicological potential and low environmental hazard.
  • Volatile organic compounds having a boiling point of ⁇ 250 ° C (VOC contents) should not be explicitly added to the aqueous pigment preparations and be present only in small amounts in the form of unreacted synthesis raw materials or as side reaction products.
  • Sulfosuccinic acid derivatives of the formula (I) in combination with nonionic surfactants fulfill this task.
  • the invention therefore relates to aqueous, binder-free
  • Pigment preparations containing (A) 1, 0 to 75.0 wt .-% of at least one organic or inorganic
  • White or colored pigment or a mixture of different organic and inorganic white or colored pigments 0.01 to 8.0% by weight of at least one compound of the formula (I),
  • R is a saturated or unsaturated, linear or branched, aliphatic or alicyclic hydrocarbon radical having 6 to 18 carbon atoms,
  • n is an integer from 0 to 10
  • A is an oxygen atom or a bifunctional group of
  • B is a hydrogen atom or a group of the formula (III),
  • X and Y are sulfonic acid groups in acid form or their sodium
  • Y is a hydrogen atom and vice versa when X is a potassium and ammonium salt and hydrogen atoms Represents hydrogen, Y is a sulfonic acid group or its salt is and
  • M is a hydrogen atom or a sodium, potassium or
  • the pigment preparation according to the invention may optionally contain one or more of the constituents
  • Pigment preparations conventional auxiliaries such as additional wetting agents, humectants, solvents, defoamers, rheology additives,
  • Preservatives, buffer substances and pH regulators included.
  • the pigment preparations according to the invention are shear-resistant,
  • the component (A) of the pigment preparations of the invention is preferably a finely divided, organic or inorganic white or Colored pigment or a mixture of different pigments.
  • organic pigments are carbon black pigments, such as. B. gas or Furnaceruße; Monoazo and
  • Disazo pigments in particular the Color Index pigments Pigment Yellow 1, Pigment Yellow 3, Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 16, Pigment Yellow 17, Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 81, Pigment Yellow 83 , Pigment Yellow 87, Pigment Yellow 97, Pigment Yellow 111, Pigment Yellow 126, Pigment Yellow 127, Pigment
  • Benzimidazoline pigments in particular the Color Index pigments Pigment Yellow 120, Pigment Yellow 151, Pigment Yellow 154, Pigment Yellow 175,
  • Triarylcarboniumpigmente in particular the Color Index pigments Pigment Red 169, Pigment Blue 56 or Pigment Blue 61 to call.
  • suitable inorganic pigments are titanium dioxides, zinc sulfides, zinc oxides, iron oxides, magnetites, manganese iron oxides, chromium oxides, ultramarine, nickel or chromium antimony titanium oxides, manganese titanium rutiles, cobalt oxides, mixed oxides of cobalt and aluminum, rutile mixed phase pigments, rare earth sulfides, spinels of cobalt with nickel and zinc , Spinels based on iron and chromium with copper zinc as well as manganese, bismuth vanadate and extender pigments.
  • Color Index Pigments Pigment Yellow 184, Pigment Yellow 53, Pigment Yellow 42, Pigment Yellow Brown 24, Pigment Red 01, Pigment Blue 28, Pigment Blue 36, Pigment Green 50, Pigment Green 7, Pigment Black 11, Pigment Black 33 and Pigment White 6 were used.
  • Component (B) of the pigment preparations according to the invention is a derivative of sulfosuccinic acid.
  • (B) is in one embodiment
  • R is a saturated or unsaturated, linear or branched
  • n is an integer from 0 to 10
  • X and Y represent a sulfonic acid group -SO 3 M, wherein when X is a
  • Y is a hydrogen atom and, conversely, when X represents a hydrogen atom, Y is a sulfonic acid group, and
  • M represents a hydrogen atom or a sodium, potassium or ammonium ion
  • (B) in another embodiment is an alkylsulfosuccinamate of the formula (V)
  • R is a saturated or unsaturated, linear or branched
  • X and Y represent a sulfonic acid group -SO 3 M, wherein when X is a
  • Y is a hydrogen atom and, conversely, when X represents a hydrogen atom, Y is a sulfonic acid group, and
  • M represents a hydrogen atom or a sodium, potassium or ammonium ion.
  • the derivative of sulfosuccinic acid is an amide of the formula (VI) wherein
  • R is a saturated or unsaturated, linear or branched
  • M represents a hydrogen atom or a sodium, potassium or ammonium ion.
  • fatty alcohol ethoxylates di- and tristyrylphenol ethoxylates, fatty acid ethoxylates, esters of polyethylene glycols with fatty acids, fatty acid alkanolamide ethoxylates, EO / PO block copolymers, fatty alcohol EO / PO addition products, such as
  • Alcohols suitable for the preparation of the fatty alcohol ethoxylates are fatty alcohols having 8 to 22 carbon atoms of natural origin, such as octyl alcohol,
  • coconut fatty alcohol and palm kernel oil alcohol for example, coconut fatty alcohol and palm kernel oil alcohol.
  • Alkanols with 6 to 22 carbon atoms are suitable.
  • the alcohols used may be saturated and unsaturated.
  • the fatty alcohols are in a conventional manner with the aid of alkaline or acidic catalysts
  • ethylene oxide The average degree of ethoxylation of the alcohols is 1 to 100 mol of ethylene oxide, preferably 3 to 50 and more preferably 5 to 30 mol of ethylene oxide.
  • di- and Tristyrylphenolethoxylate be prepared from di- and tristyrylphenol, wherein the alcohols may be present as mixtures of mono-, di- and tristyrylphenol and the average degree of substitution of 2 to 3 may be 1-Phenylethylaughen.
  • Suitable fatty acid ethoxylates are reaction products of ethylene oxide with natural and synthetic fatty acids, which were reacted with 1 to 100 moles of ethylene oxide, preferably 3 to 50 and more preferably 5 to 30 moles of ethylene oxide.
  • Other fatty acid derivatives which are suitable for the reaction with ethylene oxide are fatty acid sorbitan esters, castor oil, fatty acid glycerol esters and
  • nonionic surfactants are esterification products of
  • Polyethylene glycol having an average molecular weight of 200 to 8000 g / mol with fatty acids.
  • Component (C) are ethoxylation products of fatty acid alkanolamides.
  • ethoxylated fatty acid ethanolamides (formula VII).
  • Ethoxylated fatty acid ethanolamides are preferably prepared by reacting fatty acids with ethanolamine to form the fatty acid ethanolamide and then adding ethylene oxide using alkaline catalysts such as sodium or potassium methylate.
  • R 1 is preferably an alkyl or alkenyl group having 11 to 19 carbon atoms, which may also contain more than one double bond
  • m is a number from 1 to 50, preferably 1 to 30 and preferably at least equal to 2, in particular at least equal 3.
  • ethylene oxide is preferably added to the terminal hydroxyl group. The addition of ethylene oxide to the nitrogen of the amide group is subordinate in a side reaction, so that subordinated to the nitrogen and 2 Polyethylenglykoletherreste are bound.
  • Suitable fatty acids for the preparation of the fatty acid ethanolamides are
  • Sunflower oil fatty acid soybean oil fatty acid or rosin acids such as tall oil fatty acid.
  • the fatty acids used as raw material can be saturated and unsaturated.
  • component (C) are nonionic surfactants
  • Ethylene oxide / propylene oxide block copolymers having an average molecular weight of preferably 1000 to 10000 g / mol and an ethylene oxide content of preferably 10 to 99 wt .-% in the molecule.
  • the ethylene oxide / propylene oxide block copolymers are prepared by addition of ethylene oxide
  • Nonionic surfactants suitable as component (C) are fatty alcohol EO / PO addition products and end-capped fatty alcohol ethoxylates. Suitable fatty alcohol EO / PO addition products are by blockwise
  • Suitable end-capped fatty alcohol ethoxylates are
  • methyl chloride for example, methyl chloride, ethyl chloride and n-butyl chloride.
  • Component (D) is a clay mineral thickener based on natural or alkaline activated montmorillonite phyllosilicate minerals.
  • Montmorillonite is the essential ingredient of bentonite and has a high content
  • Pigment preparation according to the invention may be added to slow down or prevent the settling of organic and inorganic pigments and fillers and the syneresis, that is the formation of a second phase of different composition.
  • Component (E) is an inorganic filler which can be added to the pigment preparations according to the invention in order to increase the density and to change the flow behavior. At volumetric dosage and lower
  • Pigment concentration or light organic pigments it may be possible that the pigment preparation in the dispensers can be metered only poorly, because the gravitational force is insufficient to empty the liquid pigment preparation in the paint container. In other cases, the viscosity of the pigment preparations is too low at low pigment concentrations, resulting in dripping. In both cases, the inventive
  • Colorless inorganic fillers can be added to pigment preparations in order to increase the density of the pigment preparation and to improve the flow behavior.
  • Suitable fillers are calcium carbonates such as naturally occurring chalk and precipitated calcium carbonate, dolomite, natural silica (quartz powder), pyrrole and precipitated silicas, diatomaceous earth, aluminas,
  • the components (F) are further for the preparation of aqueous
  • Pigment preparations conventional auxiliaries such as additional wetting agents,
  • Preservatives buffer substances and pH regulators.
  • Additional wetting agents may be wetting agents based on polysiloxane ethers, for example a methoxypolyethoxypropyltrisiloxane, alkynediolethoxylates and fluorosurfactants.
  • Suitable humectants and solvents are preferably glycol ethers, which are understood here to mean compounds having ethoxy and / or propoxy groups which have average molecular weights of from 200 to 20,000 g / mol, in particular polyethylene glycol ethers or polypropylene glycol ethers having an average molar mass of from 200 to 20,000 g / mol, mono , Di- or
  • Triethylene glycol mono-, di- or tripropylene glycol, methyl, ethyl-propyl, butyl or higher alkylpolyalkylene glycol ethers having 1, 2, 3 or more
  • Ethylene glycol or propylene glycol units such as, for example, methoxypropanol, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether,
  • Glycerol ethoxylates having a molecular weight of from 200 to 20,000 g / mol
  • pentaerythritol alkoxylates having a molecular weight of from 200 to 20,000 g / mol
  • further ethoxylation and alkoxylation products and random or block copolymers prepared by addition of ethylene oxide and / or propylene oxides to monohydric and higher alcohols were, with a molecular weight of 200 to 20,000 g / mol.
  • Information on molecular weights of polymers always refer to their number average molecular weight, unless otherwise specified in individual cases. Molecular weights are to be determined by GPC against polyethylene glycol as standard.
  • Pigment preparations are preferably water-soluble organic or hydrotropic substances which optionally also serve as solvents.
  • Tetramethylurea Tetramethylurea, ⁇ -caprolactam, glycerol, diglycerol, polyglycerol,
  • Suitable defoamers are preferably mineral oil defoamers and their emulsions, silicone oil defoamers and silicone oil emulsions, polyalkylene glycols, polyalkylene glycol fatty acid esters, fatty acids, higher-value alcohols,
  • Phosphoric acid ester hydrophobically modified silica, aluminum tristearate,
  • Suitable further rheology additives as viscosity regulators are e.g. Starch and cellulose derivatives and hydrophobically modified ethoxylated urethanes (HEUR) thickeners, alkali-swellable acrylate thickeners, hydrophobically modified acrylate thickeners, polymers of acrylamidomethylpropanesulfonic acid or pyrogenic silica.
  • HEUR hydrophobically modified ethoxylated urethanes
  • Pot preservatives are added to stabilize the aqueous pigment preparations and to prevent the uncontrolled proliferation of bacteria, algae and fungi.
  • Suitable biocides are formaldehyde, formaldehyde-releasing components, methylisothiazolinone, chloromethylisothiazolinone,
  • organic or inorganic bases and acids are used.
  • Preferred organic bases are amines, such as. Ethanolamine, diethanolamine, triethanolamine,
  • Water used to prepare the aqueous pigment preparations according to the invention, component (G), is preferably used in the form of distilled or demineralized water. Also drinking water (tap water) and / or water of natural origin can be used. Water is preferably contained in the aqueous pigment preparation according to the invention to 10 to 75 wt .-%, in particular ad 100 wt .-%.
  • the aqueous pigment preparations according to the invention preferably have a viscosity of 0 to 10,000 mPas, preferably 30 to 5,000 mPas and particularly preferably 50 to 3,000 mPas, measured with a cone-and-plate viscometer at a shear rate of 1/60 sec -1 , e.g. a Haake
  • Viscometer 550 measured.
  • aqueous pigment preparations of the invention are in each
  • the present invention also provides a process for the preparation of the pigment preparations according to the invention by reacting component (A) in the form of powder or granules in the presence of water (G) and the
  • the liquid components (B), (C), (G) and optionally (F) are mixed and homogenized, then the solid, powdered, granulated or flaky component (A), (D) and (E) and in the submitted Mixture stirred, the pigment and
  • the fillers are pasted and predispersed. Depending on the grain hardness of the pigments used, it is then optionally finely dispersed or finely divided with cooling with the aid of a grinding or dispersing unit.
  • agitators dissolvers (sawtooth stirrers), rotor-stator mills, ball mills, stirred ball mills such as sand and pearl mills,
  • Range from 0 to 100 ° C, advantageously at a temperature between 10 and 70 ° C, preferably at 20 to 60 ° C.
  • the pigment preparation can be further diluted with water, preferably deionized or distilled water.
  • the pigment preparations according to the invention are suitable for pigmenting and dyeing macromolecular materials of all kinds.
  • the pigment preparation according to the invention are suitable for pigmenting or producing paints and dispersion paints, dispersion paints, printing inks, in this case for example textile printing inks, flexographic printing inks, decor printing or gravure printing inks, wallpapers waterborne lacquers, wood stains, wood protection systems and lacquers for the surface coating of objects made of, for example, metal, wood, plastic, glass, ceramic, concrete, textile material, paper or
  • a special property of the pigment preparations according to the invention is their use as universal tinting pastes.
  • Universal tinting pastes are suitable both for coloring aqueous paints and tinting solvent-based paints.
  • Pigment preparations stabilize the pigments only in aqueous, but not in solvent-based systems. Become aqueous pigment preparations for
  • Dyeing of solvent-based paints can lead to agglomeration of the pigments and cause floating of the agglomerated pigments in the paint.
  • Spray application can cause streakiness and a disturbed color image due to hue differences, because the pigments flocculate in the paint and during the drying process, so that the color strength is reduced.
  • the pigment agglomerates are separated again, but with different strengths, so that they are observed
  • the pigment either as a powder, granules or as a press cake, is made into a paste together with the dispersants and the other additives in deionized water and then mixed with a dissolver (for example from VMA Getzmann GmbH, type AE3-M1) or a homogenized and predispersed to other suitable apparatus.
  • a dissolver for example from VMA Getzmann GmbH, type AE3-M1
  • a homogenized and predispersed to other suitable apparatus for example from VMA Getzmann GmbH, type AE3-M1
  • liquid components (B), (C) and (F) are placed in a grinding container and mixed. Subsequently, the liquid components (B), (C) and (F) are placed in a grinding container and mixed. Subsequently, the liquid components (B), (C) and (F) are placed in a grinding container and mixed. Subsequently, the liquid components (B), (C) and (F) are placed in a grinding container and mixed. Subsequently, the
  • powdered components (A) and optionally (D) and (E) are added and predispersed with the dissolver.
  • the subsequent fine dispersion takes place with the aid of a bead mill (for example with AE3-M1 from VMA-Getzmann) or another suitable one
  • the pigment preparation is stored at 60 ° C for one week and visually assessed.
  • the viscosity of the pigment preparation is at 25 ° C with a Haake Viscometer 550 at a shear rate of 1/60 sec "1 or at good flowable
  • Pigment preparations measured with a Brookfield viscometer, Model DV-II with spindle 3 at 100 rpm. To determine the color strength and the compatibility, the pigment preparations are each an aqueous
  • Disperse white color and a mineral oil-containing long oil alkyd varnish added.
  • 200 g each of the tinted colors consisting of 92% by weight of basecoat and 8% by weight of the pigment preparation, are placed in a tin can and held for 60 seconds
  • the tinted colors are after one day on a test cardboard with a 120 ⁇ doctor blade on a film-drawing device, model 509 MC Fa. Erichsen GmbH, Hemer
  • component (B) in analogy to formula (V)) 5.0 parts of oleyl ethoxylate reacted with 8 moles of ethylene oxide (Genapol ® O 080,
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 1.8 Pas, measured with a Haake cone-plate viscometer.
  • the dispersion white color tinted with the pigment paste and the long oil alkyd paint show no rubout. After further storage for 4 weeks at 25 ° C, the pigment preparation remains homogeneous and suitable for use as a tinting paste.
  • the pigment preparation after grinding is a liquid, viscous pigment dispersion.
  • the pigment preparation becomes solid after 1 week storage at 60 ° C and strongly thixotropic.
  • the paste liquefies again and has a pigment preparation viscosity of 3.80 Pa s as measured with a Haake cone-and-plate viscometer. Repeated storage thickens the
  • Dispersion white paint shows no rubout, whereas the long oil alkyd paint tinted with the pigment paste shows a strong rubout.
  • the pigment preparation after grinding is a liquid, viscous
  • Pigment dispersion The pigment preparation is solid after storage for one week at 60 ° C. The viscosity can not be determined and the pigment preparation is unsuitable for the liquid dosing as a tinting paste.
  • Example 4 Comparative Example
  • the pigment preparation after grinding is a liquid, viscous dispersion.
  • the pigment preparation is liquid after one week storage at 60 ° C, viscous and the viscosity is 4.0 Pa s measured with a Haake cone plate Viscometer at a shear rate of 1/60 sec 1 .
  • the disperse white pigment tinted with the pigment preparation shows no rubout, whereas the long oil alkyd paint tinted with the pigment paste shows a strong rubout.
  • the pigment preparation thickens and is then no longer suitable for use as a tinting paste of paints and inks.
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 2.9 Pa s, measured with a Haake cone-plate viscometer.
  • the dispersion white color tinted with the pigment paste and the long oil alkyd paint show no rubout. After further storage for 4 weeks at 25 ° C, the pigment preparation remains homogeneous and suitable for use as a tinting paste.
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 0.92 Pa s, measured with a Haake cone-plate viscometer.
  • the dispersion white color tinted with the pigment paste and the long oil alkyd paint show no rubout. After further storage for 4 weeks at 25 ° C, the pigment preparation remains homogeneous and suitable for use as a tinting paste.
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 1.02 Pa s, measured with a Haake cone-plate viscometer.
  • the dispersion white color tinted with the pigment paste and the long oil alkyd paint show no rubout.
  • the pigment preparation is separated into 2 phases, but can be homogenized by stirring or shaking and is then suitable for use as a tinting paste.
  • Example 8 50.0 parts of Cl Pigment Black 11 (Bayferrox Black 316, Lanxess,
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 1.3 Pa s, measured with a Haake cone-plate viscometer.
  • the dispersion white color tinted with the pigment paste and the long oil alkydiack show no rubout.
  • the pigment preparation remains homogeneous and suitable for use as a tinting paste.
  • component (B) Fa. Clariant, component (B)), 8.0 parts of tallow fatty acid ethanolamide reacted with 10 moles of ethylene oxide (component (C)),
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 0.5 Pa s, measured with a Haake cone-plate viscometer.
  • the dispersion white color tinted with the pigment paste and the long oil alkyd paint show no rubout.
  • the pigment preparation is separated into 2 phases, but can be homogenized by stirring or shaking and is then suitable for use as a tinting paste.
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 0.22 Pa s, measured with a Haake cone-and-plate viscometer.
  • the dispersion white color tinted with the pigment paste and the long oil alkyd paint show no rubout.
  • the pigment preparation is separated into 2 phases, but can be homogenized by stirring or shaking and is then suitable for use as a tinting paste.
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 0.24 Pa s, measured with a Haake cone-and-plate viscometer.
  • the dispersion white color tinted with the pigment paste and the long oil alkyd paint show no rubout.
  • the pigment preparation is separated into 2 phases, but can be homogenized by stirring or shaking and is then suitable for use as a tinting paste.
  • Example 12 60.0 parts of Cl Pigment Black 1 l (Bayferrox Black 316, Lanxess,
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 1.17 Pa s, measured with a Haake cone-plate viscometer.
  • the dispersion white color tinted with the pigment paste and the long oil alkydiack show no rubout. After further storage for 4 weeks at 25 ° C, the pigment preparation remains homogeneous and suitable for use as a tinting paste.
  • component (B) Fa. Clariant, component (B)), 8.0 parts of tallow fatty acid ethanolamide reacted with 15 moles of ethylene oxide
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 0.64 Pa s, measured with a Haake cone-plate viscometer.
  • the dispersion white color tinted with the pigment paste and the long oil alkydiack show no rubout.
  • the pigment preparation is separated into 2 phases, but can be homogenized by stirring or shaking and is then suitable for use as a tinting paste.
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 1.19 Pa s, measured with a Haake cone-plate viscometer.
  • the dispersion white color tinted with the pigment paste and the long oil alkyd paint show no rubout. After further storage for 4 weeks at 25 ° C, the pigment preparation remains homogeneous and suitable for use as a tinting paste.
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 0.22 Pa s, measured with a Haake cone-and-plate viscometer.
  • the dispersion white color tinted with the pigment paste and the long oil alkyd paint show no rubout.
  • the pigment preparation is separated into 2 phases, but can be homogenized by stirring or shaking and is then suitable for use as a tinting paste.
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 0.81 Pa s, measured with a Haake cone-plate viscometer.
  • the dispersion white pigment tinted with the pigment paste and the long oil alkyd paint show no rubout.
  • the pigment preparation is separated into 2 phases, but can be homogenized by stirring or shaking and is then suitable for use as a tinting paste.
  • component (B) Fa. Clariant, component (B)), 5.2 parts of oleyl ethoxylate with 8 moles of ethylene oxide (Clariant Genapol ® O 080, Fa.,
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 175 mPa.s, measured with a Brookfield viscometer using spindle 3 at 100 rpm.
  • the dispersion white color tinted with the pigment paste and the long oil alkydiack show no rubout.
  • the pigment preparation remains homogeneous and suitable for use as a tinting paste.
  • Example 18 5.0 parts C.I. Pigment Black 7 (Special Black 4, Evonik,
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 162 mPa.s, measured with a Brookfield viscometer using spindle 3 at 100 rpm.
  • the dispersion white color tinted with the pigment paste and the long oil alkyd paint show no rubout.
  • the pigment preparation remains homogeneous and suitable for use as a tinting paste.
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 82 mPa.s, measured with a Brookfield viscometer by means of spindle 3 at 100 rpm.
  • the dispersion white color tinted with the pigment paste and the long oil alkydiack show no rubout.
  • the pigment preparation remains homogeneous and suitable for use as a tinting paste.
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 183 mPa s, measured with a Brookfield viscometer by means of spindle 3 at 100 rpm.
  • the dispersion white color tinted with the pigment paste and the long oil alkyd paint show no rubout.
  • the pigment preparation remains homogeneous and suitable for use as a tinting paste.
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free.
  • the viscosity of the pigment preparation is 0.38 Pa s, measured with a Haake cone-and-plate viscometer at a shear rate of 1/60 sec.sup.- 1 .
  • the disperse white pigment tinted with the pigment paste shows no rubout, whereas the long oil alkyd paint tinted with the pigment paste After further storage for 4 weeks at 25 ° C, the pigment preparation remains homogeneous and suitable for use as a tinting paste for waterborne paints.
  • Example 22 Comparative Example
  • defoamer D-Foam-R C 740, Fa. Clariant, component (F)
  • a preservative Nipacide ® BSM, Fa. Clariant
  • the pigment preparation After one week of storage at 60 ° C., the pigment preparation is pasty and highly viscous and can not be dosed as a tinting paste.
  • Pigment preparation is outside the measuring range of the usual measuring instruments, can not be determined.
  • Pigment preparations with suitable viscosity can be combined with the
  • Components B and C contain a good compatibility and no rubout when tinting aqueous and solventborne paints and inks.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

L'invention concerne des préparations aqueuses de pigments qui sont exemptes de liants et qui contiennent (A) 1,0 à 75,0 % en poids d'au moins un pigment blanc ou coloré de nature organique ou inorganique, ou un mélange de différents pigments blancs ou colorés de nature organique ou inorganique, (B) 0,01 à 8,0 % en poids d'au moins un composé de formule (I) dans laquelle R est un radical hydrocarboné aliphatique ou alicyclique, linéaire ou ramifié, saturé ou insaturé, renfermant 6 à 18 atomes de carbone; n est un nombre entier compris entre 0 et 10; A est un atome d'oxygène ou un groupe bifonctionnel de formule (II), B est un atome d'hydrogène ou un groupe de formule (III) dont la liaison est réalisée par la valence indiquée par *, X et Y sont choisis parmi les groupes d'acide sulfonique sous leur forme acide ou sous forme de leur sel de sodium, de potassium et d'ammonium et parmi les atomes d'hydrogène, Y étant un atome d'hydrogène si X est un groupe d'acide sulfonique ou un sel de ce dernier et, inversement, Y étant un groupe d'acide sulfonique ou un sel de ce dernier et M représentant un atome d'hydrogène ou un ion de sodium, de potassium ou d'ammonium si X est un atome d'hydrogène, et n étant égal à 0 et M représentant un atome de sodium si B est un groupe fonctionnel de formule (III), (C) 0,01 à 12,0 % en poids d'un tensioactif non-ionique, et (G) étant de l'eau.
EP13753812.0A 2012-09-19 2013-08-20 Dérivés de l'acide sulfosuccinique servant d'agent de dispersion dans des préparations de pigments exemptes de liants Not-in-force EP2898021B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102012018544.8A DE102012018544A1 (de) 2012-09-19 2012-09-19 Derivate der Sulfobernsteinsäure als Dispergiermittel in bindemittelfreien Pigmentpräparationen
PCT/EP2013/002503 WO2014044345A1 (fr) 2012-09-19 2013-08-20 Dérivés de l'acide sulfosuccinique servant d'agent de dispersion dans des préparations de pigments exemptes de liants

Publications (2)

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EP2898021A1 true EP2898021A1 (fr) 2015-07-29
EP2898021B1 EP2898021B1 (fr) 2017-02-01

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EP13753812.0A Not-in-force EP2898021B1 (fr) 2012-09-19 2013-08-20 Dérivés de l'acide sulfosuccinique servant d'agent de dispersion dans des préparations de pigments exemptes de liants

Country Status (6)

Country Link
US (1) US9187619B2 (fr)
EP (1) EP2898021B1 (fr)
DE (1) DE102012018544A1 (fr)
ES (1) ES2617205T3 (fr)
PT (1) PT2898021T (fr)
WO (1) WO2014044345A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012013046A1 (de) * 2012-06-29 2014-01-02 Clariant International Ltd. Fettsäurekondensationsprodukte als Dispergiermittel in Pigmentpräparationen
US9390858B2 (en) * 2014-04-03 2016-07-12 Murata Manufacturing Co., Ltd. Electronic component, method of manufacturing the same, and mount structure of electronic component
FI127636B (en) * 2017-04-13 2018-11-15 Tikkurila Oyj A water-based general tinting composition and method for tinting a base paint
CN108587434A (zh) * 2018-06-01 2018-09-28 江苏清陶能源科技有限公司 一种提高稳定性以及避免固体组分沉降的涂料及其制备方法
BR112022004350A2 (pt) * 2019-10-08 2022-05-31 Swimc Llc Composição de corante de madeira
EP4011987A1 (fr) * 2020-12-10 2022-06-15 Clariant International Ltd Sel d'amidat d'acide gras n,n-dialkyl(sulfooxy) comme dispersant pour les préparations pigmentaires

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Publication number Priority date Publication date Assignee Title
BE785705A (fr) * 1971-06-30 1973-01-02 Hoechst Ag Semi-esters de l'acide sulfo-succinique utilisables dans des preparations pigmentaires
BE785703A (fr) * 1971-06-30 1973-01-02 Hoechst Ag Dispersions de colorants
BE794155A (fr) 1972-01-20 1973-07-17 Bayer Ag Pigments colores mineraux
US4169737A (en) * 1976-08-06 1979-10-02 Marion Darrah And Joseph Y. Houghton, Co-Trustees Intrachromospheruloid/intraleuco-spheruloid pigment compositions and processes for producing same
DE2638946C3 (de) * 1976-08-28 1983-06-16 Hoechst Ag, 6230 Frankfurt Pigmentdispersionen für den Einsatz in hydrophilen und hydrophoben Medien
DE3729657A1 (de) * 1987-09-04 1989-03-23 Hoechst Ag Harzsaeureester auf basis von novolakoxalkylaten, ihre herstellung und verwendung
EP0403718A3 (fr) * 1989-06-20 1991-12-27 Ciba-Geigy Ag Produits dérivés de l'oxyde de styrène
GB9116240D0 (en) * 1991-07-27 1991-09-11 Ciba Geigy Ag Pigment compositions
ES2134231T3 (es) * 1992-08-11 1999-10-01 Clariant Gmbh Compuestos tensioactivos a base de sustancias grasas de aceite de ricino modificadas.
DE10252452B4 (de) * 2002-11-12 2006-07-06 Clariant Gmbh Styroloxidhaltige Copolymere und deren Verwendung als Emulgatoren und Dispergiermittel
DE10350556A1 (de) * 2003-10-29 2005-06-02 Clariant Gmbh Wasserbasierende Pigmentpräparationen
DE102004051455A1 (de) * 2004-10-22 2006-04-27 Clariant Gmbh Wasserbasierende Pigmentpräparationen auf Oligoesterbasis, ihre Herstellung und Verwendung
GB0516860D0 (en) * 2005-08-17 2005-09-21 Ici Plc A dry pigment blend
DE102006002800A1 (de) * 2006-01-20 2007-08-02 Clariant International Limited Dispergiermittel für wässrige Pigmentpräparationen
DE102007045230A1 (de) * 2007-09-21 2009-04-09 Clariant International Limited Polycarboxylatether als Dispergiermittel für anorganische Pigmentformulierungen
CN102575111A (zh) * 2009-06-12 2012-07-11 日本化药株式会社 四氮杂卟啉色素、油墨组合物、记录方法以及着色体
WO2011024855A1 (fr) * 2009-08-26 2011-03-03 Dic株式会社 Procédé de production d'une encre aqueuse pour l'impression par jet d'encre et d'une dispersion de pigment liquide du type aqueux
US8968462B2 (en) * 2012-01-13 2015-03-03 Clariant Finance (Bvi) Limited Inorganic pigment dispersions containing fatty acid ethanol amide ethoxylates and amines
DE102012013046A1 (de) * 2012-06-29 2014-01-02 Clariant International Ltd. Fettsäurekondensationsprodukte als Dispergiermittel in Pigmentpräparationen
DE102013016889B4 (de) * 2013-10-11 2016-10-13 Clariant International Ltd. Wässrige, bindemittelfreie Pigmentpräparationen und deren Verwendungen

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WO2014044345A1 (fr) 2014-03-27
US9187619B2 (en) 2015-11-17
ES2617205T3 (es) 2017-06-15
EP2898021B1 (fr) 2017-02-01
PT2898021T (pt) 2017-05-11
DE102012018544A1 (de) 2014-03-20
US20150247023A1 (en) 2015-09-03

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